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Patent 2155289 Summary

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(12) Patent: (11) CA 2155289
(54) English Title: POLYURETHANE INSECTICIDAL EAR TAG METHODS OF USE AND PREPARATION
(54) French Title: PLAQUETTES D'OREILLE INSECTICIDES A BASE DE POLYURETHANE; METHODE D'UTILISATION ET PREPARATION
Status: Expired and beyond the Period of Reversal
Bibliographic Data
(51) International Patent Classification (IPC):
  • A01N 25/34 (2006.01)
  • A01K 13/00 (2006.01)
  • A01N 25/10 (2006.01)
(72) Inventors :
  • KRZEWKI, RUDOLF J. (United States of America)
  • ACKERS, STANLEY (United States of America)
(73) Owners :
  • FERMENTA ANIMAL HEALTH COMPANY
(71) Applicants :
  • FERMENTA ANIMAL HEALTH COMPANY (United States of America)
(74) Agent: SMART & BIGGAR LP
(74) Associate agent:
(45) Issued: 1998-12-01
(22) Filed Date: 1995-08-02
(41) Open to Public Inspection: 1996-02-11
Examination requested: 1996-03-14
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
08/288,598 (United States of America) 1994-08-10

Abstracts

English Abstract


A polymeric device and method for the control of
insects on animals is disclosed. The device is in the form of
an ear tag or other shape which can be attached to an animal
using known techniques. A unique polymer/insecticidal
formulation is provided by combining an ectoparasiticidal active
compound, such as one or more organophosphates, carbamates,
pyrethroids and organochlorines, with a polyurethane polymer.
The polymer is the reaction product of 4,4'-diphenylmethane
diisocyanate, polytetramethylene glycol and 1,4-butanediol. By
utilizing the particular polymers described, high loadings of
insecticides are possible and the resulting product shows no
tendency to exude insecticide during prolonged storage. The
product made according to the invention can provide effective
control of horn flies on cattle for six months or more utilizing
a single ear tag or the like where it would take two tags
constructed according to the prior art to achieve comparable
results. The result is lower costs in product and labor, greater
safety to an animal and workers and a lower quantity of residual
product to dispose.


French Abstract

Divulgation d'un dispositif polymérique et d'une méthode de lutte contre les insectes nuisibles aux animaux. Le dispositif a la forme d'une plaquette d'oreille ou une autre forme que l'on peut attacher à un animal au moyen de techniques connues. L'invention fournit une formulation unique de polymère et d'insecticide obtenue par la combinaison d'un composé actif ectoparasiticide, comme un ou plusieurs composés organophosphorés, des carbamates, des pyréthroïdes et des organochlorés, avec un polyuréthane (polymère). Le polymère est le produit de la réaction du diisocyanate-4,4' de diphénylméthane, du polytétraméthylèneglycol et du 1,4-butanediol. En utilisant les polymères particuliers décrits, il est possible d'avoir de fortes charges d'insecticide sans que le produit résultant n'exsude de l'insecticide pendant une période de conservation prolongée. Le produit fabriqué selon l'invention lutte efficacement, pendant six mois ou plus, contre la mouche des cornes nuisible aux bovins au moyen d'une simple plaquette d'oreille ou d'un dispositif semblable, alors qu'il faudrait deux plaquettes produites selon les méthodes déjà existantes pour obtenir des résultats comparables. Les coûts des produits et de main-d'oeuvre sont ainsi réduits, le produit est plus sûr pour les animaux, et la quantité de produit résiduel à éliminer est moindre.

Claims

Note: Claims are shown in the official language in which they were submitted.


- 34 -
THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A device for protecting animals from insects, said
device comprising:
30% to 80% by weight of a polyurethane polymer which is
the reaction product of 20% to 40% by weight
4,4'-diphenylmethane diisocyanate, 50% to 70% by weight
polytetramethylene glycol and 2% to 10% by weight,
1,4-butanediol and has a number average molecular weight of not
less than about 90,000, said polymer being formed into a shape
for attachment to said animals; and
20% to 70% by weight of an ectoparasiticidal active
compound absorbed into and releasable from said polymer and
selected from the group consisting of pyrethroids,
organochlorines and carbamates.
2. The device as set forth in claim 1 wherein the
ectoparasiticidal active compound is selected from the group
consisting of pyrethroids, endosulfan and methoxychlor.
3. The device as set forth in claim 1 or 2, including
up to 20% by weight polyvinyl chloride.
4. The device as set forth in any one of claims 1 to 3,
comprising 40% to 60% by weight polymer and 30% to 60% by
weight ectoparasiticidal active compound.

- 35 -
5. The device as set forth in any one of claims 1 to 4,
comprising approximately 46% by weight polymer, approximately
46% by weight ectoparasiticidal active compound, approximately
6% by weight polyvinyl chloride and 2% by weight inert
ingredients.
6. The device as set forth in any one of claims 1 to 5,
wherein said polymer has a Shore hardness of between 70 and 90
A units.
7. The device as set forth in any one of claims 1 to 6,
wherein said polymer is shaped to form an ear tag.
8. The device as set forth in any one of claims 1 to 7,
wherein the ectoparasiticidal active compound is endosulfan or
methoxychlor.
9. The device as set forth in any one of claims 1 to 8,
wherein said ectoparasiticidal active compound is a
pyrethroid.
10. The device as set forth in any one of claims 1 to 9
wherein said ectoparasiticidal active component is selected
from two or more of the group consisting of pyrethroids,
carbamates and organochlorines.
11. A method for preparing a device for protecting
animals from insects, said method comprising combining 30% to

- 36 -
80% by weight of a polyurethane polymer which is the reaction
product of 20% to 40% by weight 4,4'-diphenylmethane
diisocyanate, 50% to 70% by weight polytetramethylene glycol
and 2% to 10% by weight 1,4-butanediol and has a number
average molecular weight of not less than about 90,000, said
polymer being formed into a shape for attachment to said
animals; and
20% to 70% by weight of an ectoparasiticidal active
compound absorbed into and releasable from said polymer and
selected from the group consisting of pyrethroids,
organochlorines and carbamates; and forming the combination
into a device which is attachable to an animal and from which
said ectoparasiticidal active compound is releasable to
protect said animal from insects.
12. The method as set forth in claim 10, wherein the
ectoparasiticidal active compound is selected from the group
consisting of pyrethroids, endosulfan and methoxychlor.
13. The method as set forth in claim 11 or 12, wherein
said device includes up to 20% by weight polyvinyl chloride.
14. The method as set forth in claim 11, 12 or 13
wherein said device comprises 40% to 60% by weight polymer and
30% to 60% by weight ectoparasiticidal active compound.
15. The method as set forth in any one of claims 11 to
14, wherein said polymer has a Shore hardness of between 70

- 37 -
and 90 A units.
16. The method as set forth in any one of claims 11 to
15 wherein the combination of polymer and ectoparasiticidal
active compound is shaped to form an ear tag.
17. A method of protecting non-human domestic animals
from insects, said method comprising: attaching to the animal
a device comprising 30% to 80% by weight of a polyurethane
polymer which is the reaction product of 20% to 40% by weight
4,4'-diphenylmethane diisocyanate, 50% to 70% by weight
polytetramethylene glycol and 2% to 10% by weight
1,4-butanediol and has a number average molecular weight of not
less than about 90,000, said polymer being formed into a shape
for attachment to said animals; and
20% to 70% by weight of an ectoparasiticidal active
compound absorbed into and releasable from said polymer and
selected from the group consisting of pyrethroids,
organochlorines and carbamates; the ectoparasiticidal active
compound being in association with and releasable from the
polymer to protect said animal from insects.
18. The method as set forth in claim 17, wherein the
ectroparasiticidal active compound is selected from the group
consisting of pyrethroids, endosulfan and methoxychlor.
19. The method as set forth in claim 17 or 18, wherein
said device includes up to 20% by weight polyvinyl chloride.

- 38 -
20. The method as set forth in claim 17, 18 or 19,
wherein said device comprises 40% to 60% by weight polymer and
30% to 60% by weight ectoparasiticidal active compound.
21. The method as set forth in any one of claims 17 to
20, wherein said polymer has a Shore hardness of between 70
and 90 A units.
22. The method as set forth in any one of claims 17 to
21, wherein said device is an ear tag.
23. The method as set forth in any one of claims 17 to
22, wherein said animal is a bovine or ovine animal.
24. The method as set forth in any one of claim 17 to
22, wherein said animal is a porcine animal.

Description

Note: Descriptions are shown in the official language in which they were submitted.


, 2lss289
POLY~RBTHANB IN8ECTICIDAL BAR TAG
NBTHOD8 OF U8B AND PRBPARATION
Back~ o~ Of The Invention
This invention relates generally to insecticidal
protective devices for non-human domestic animals and, in
particular, to a tag or other device formed from a polyurethane
polymer having an ectoparasiticidal active compound within the
polymer matrix.
It has long been known that devices such as ear tags
impregnated with insecticide are an effective means for providing
control of horn flies and other insects on domestic livestock,
particularly cattle. The most common material for formulating
insecticidal animal tags has heretofore been polyvinyl chloride.
In recent years, concern from ecological and human safety view-
points have been raised with regard to utilizing plasticized
polyvinyl chloride on animals intended for human consumption.
Also, since polyvinyl chloride must be plasticized to perform
satisfactorily as a tag, the quantity of active insecticide which
can be incorporated into the product is reduced in direct propor-
tion to the quantity of plasticizer required.
Another disadvantage of present insecticidal tagformulating techniques is that the high loadings of plasticizer
and insecticide cause the completed product to exude or "bleed"
insecticide. This makes an unacceptable commercial product which
requires special packaging to accommodate a relatively long shelf
life, necessitates avoiding high temperatures in transport and
storage, and demands special handling requirements when the
product is removed from the package for application to an animal.

2155289
- 2 -
The use of various polyurethanes as a polymer matrix
for insecticidal animal collars has been disclosed in U.S. Patent
No. 4,189,467 to von Bittera et al. Loadings of up to 25% by
weight of an ectoparasiticidal carbamate in the polyurethane
collar were described by von Bittera et al. While these loadings
are generally acceptable for many intended applications, higher
loadings would nonetheless be desirable in order to reduce the
weight and size of the collar.
It has also been previously known to utilize
polyurethane resins for forming identification (I.D.) tags for
animals. It is further known to attach to a polyurethane I.D.
tag a porous or semi-permeable membrane in the form of a cell for
holding a reservoir of insecticide. These membranes are made of
a variety of different polymers including polyurethane. Their
construction is shown and described in U.S. Patent No. 4,562,794.
The purported advantage to utilizing such a membrane is to
provide greater control over the uniformity of release rate of
the insecticide and higher insecticide depletion than can be
obtained when the insecticide is within the polymer matrix. Some
of the polymers which have heretofore been utilized for tags of
the type contemplated by the referenced patent would not,
however, permit sufficiently high loadings of insecticide to
achieve a satisfactory tag by blending directly with an
ectoparasiticidal compound. Inherently, this known construction
is costly to manufacture because of the complicated steps of
forming and filling the cell as well as making the mechanical
fastener for joining the cell to the tag. Also, there is a

ZIS~28~
higher than desirable incidence of product failure because of the
membranes being punctured while in use on animals.
8ummary of the Invention
It is therefore an object of the present invention to
provide an insecticidal animal protective tag which will accommo-
date a higher degree of loading of the insecticidal compound than
previously known tags, thereby enhancing the effectiveness of the
tag and ext~n~;ng its useful life.
Another object of this invention is to provide an
insecticidal animal protective tag and method of preparing same
which minimizes insecticide bleeding, thereby improving the shelf
life of the product while reducing the risk of contamination by
humans handling the ear tags.
Another one of the objects of this invention is to
minimize environmental and health concerns regarding insecticidal
tag devices by utilizing a polymeric matrix which is generally
recognized as being environmentally safe and non-threatening to
humans and does not require the addition of potentially dangerous
plasticizers.
It is also an object of this invention to provide a
method of protecting animals from insects, which is more environ-
mentally safe and presents fewer health risks than existing
practices.
It is a further object of this invention to provide a
single insecticide ear tag which is as effective as two prior art
tags using the same active compound so that a single ear tag can
be used to provide the same level of protection as two

2lss28~
conventional tags.
It is a still further object of this invention to
provide a device, such as an ear tag, having high loadings of an
ectoparasiticidal component so that smaller and lighter tags can
be used to provide insect control for smaller and younger animals
such as sheep and calves which have an ear size which cannot
support higher weight ear tags without causing undesirable
physical changes to the ear.
These and other objects of the invention will be made
clear or become apparent from the following specification and
claims.
The foregoing objects are achieved by an insecticidal
tag-like device comprising an ectoparasiticidal component that
is blended with a polymer which is the reaction product of 4,4'-
diphenylmethane diisocyanate, polytetramethylene glycol and
1,4-butanediol. The invention also encompasses a method of
preparing such a device by combining the ectoparasiticidal
composition with the afore-described polymer.
The invention further encompasses a method of
protecting non-human domestic animals from ectoparasites by
attaching to the animal a device, such as an ear tag, comprising
an ectoparasiticidal effective quantity of an ectoparasiticidal
compound within a polymer matrix which is the reaction product
of 4,4'-diphenylmethane diisocyanate, polytetramethylene glycol
and 1,4butanediol.
In one aspect of the invention, the ectoparasiticidal
component used in the devices comprises an organophosphate. In

- 21 S~289
another aspect of the invention, the ectoparasiticidal component
comprises one or more carbamates, pyrethroids, and organo-
chlorines, including in combination with an organophosphate.
Notably, high loadings of the ectoparasiticidal component can be
achieved in the devices of the present invention, including
loadings of up to 70% by weight based on the total weight of the
device.
Detailed Description of the Preferred Fmhodiments
In accordance with the present invention, an
insecticidal device is provided for use in protecting non-human
domestic animals from ectoparasites. The device comprises an
ectoparasiticidal active amount of a compound in association with
a polyurethane resin.
The polyurethane resins which are useful in the present
invention are polyurethane aromatic polyether elastomers,
specifically the polymers which are the reaction product of 4,4'-
diphenylmethane diisocyanate, polytetramethylene glycol and 1,4-
butanediol. These resins generally conform to Chemical Abstracts
Service Registry Number CAS 9018-04-6. Such polymers can be
formed by polymerization of the diisocyanate with glycol
according to the following reactions:

21 S~2~9
The moieties of the polymerization reaction will
generally be present within the ranges of 20% to 40%
diisocyanate, 50% to 70% glycol, and 2% to 10% butanediol (all
by weight). It should be understood that the invention is not
limited to ear tags and could take the form of a tail tag, ear
clip, leg bracelet, collar, horse strip, medallion, chain tag or
other device which could be attached to an animal. The final
polymer will have a Shore hardness of 70-so A units, a number
average molecular weight which is not less than about 90,000, and
a melting range within the range of about 70C to 190C.
The following commercial resin products, all meeting
the foregoing criteria, have been confirmed as satisfying the
objectives of the invention and will be referred to hereinafter
by the reference letters A through H:
Reference
Letter Trademark Manufacturer
A Texin 985 A Mobay Chemical
Pittsburgh, PA USA
B Morthane PE-90 Morton Thiokol, Inc.
Chicago, IL USA
C Estane 98315 B.F. Goodrich Co.
Cleveland, OH USA
D Morthane PE-50 Morton Thiokol, Inc.
Chicago, IL USA
E Elastollan 1180A BASF Corp.
Parsippany, NJ USA
F Pellethane 2103-80A Dow Chemical
Midland, MI USA
G Elastollan 1185A BASF Corp.
Parsippany, NJ USA
H Pellethane 2103-70A Dow Chemical
Midland, MI USA

2ls~28~
Various insecticidal compositions, both liquids and
solids, can be employed in association with the polymers
described above. In one aspect of the invention, the active
compound will preferably be an ectoparasiticidal active compound
which is an organophosphate. Suitable organophosphate
insecticides include 0,0-diethyl 0-2-isopropyl-
6-methylpyrimidin-4-ylphosphorothioate, sold under thetrademark
Diazinon (Ciba-Geigy); S-1,2-bis(ethoxycarbonyl)ethyl 0,0-
dimethyl phosphorodithioate, commonly known as malathion; 0,0-
dimethyl 0-4-nitro-m-tolyl phosphorothioate, sold under the
trademark Sumithion by Sumitomo Chemical Co. Ltd,; and 0,0,0 ,0-
tetraethyl S,S-methylene bis(phosphorodithioate), commonly known
as ethion and sold by FMC, Inc.
In another aspect of the invention, the active
component will preferably be an ectoparasiticidal active compound
selected from the group consisting of one or more pyrethroids,
organochlorines and carbamates.
The pyrethroid insecticides useful in the present
invention include cyano(3-phenoxyphenyl)methyl 4-chloro-~-(1-
methylethyl)benzeneacetate, commonly known as fenvalerate, andthe active isomer thereof commonly known as esfenvalerate;
cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-
dimethyl-cyclopropanecarboxylate,commonlyknownascypermethrin;
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-
dimethylcyclopropanecarboxylate, commonly known as permethrin;
(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)-
cyclopropanecarboxylate, commonly known as phenothrine; cyano(4-

- 21 SS2~9
fluoro-3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-
dimethylcyclopropanecarboxylate, commonly known as cyfluthrin;
[1~,3a(Z)]-(i)-cyano-(3-phenoxyphenyl)methyl 3-(2-chloro-3,3,3-
trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate,
commonly known as cyhalothrine; [l~(S*),3~(Z)]-(+)-cyano-(3-
phenoxyphenyl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-
dimethylcyclopropanecarboxylate, commonly known as lambda-
cyhalotrin; cyano(3-phenoxyphenyl)methyl-2,2-dimethyl-3-(2-
methyl-l-propenyl)cyclopropanecarboxylate, commonly known as
cyphenothrin; (RS)-cyano-(3-phenoxyphenyl)methyl (S)-4-
(difluoromethoxy)-~-(1-methylethyl)benzeneacetate, commonly known
as flucythrinate; cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-
(1,2,2,2-tetrabromoethyl)cyclopropanecarboxylate,commonlyknown
as tralomethrin; and [1~,3~(Z)]-(+)-(2-methyl[1,1'-biphenyl]-3-
yl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-
dimethylcyclopropanecarboxylate, commonly known as bifenthrin.
The organochlorines useful in this invention include
endosulfan, also known as C,C'-(1,4,5,6,7,7-hexachloro-8,9,10-
trinorborn-5-en-2,3-ylene)(dimethyl sulfite) and methoxychlor,
also known as 1,1,1-trichloro-2,2-bis(4-methoxyphenyl)ethane.
The carbamates can include 2,3-dihydro-2,2-
dimethylbenzofuran-7-yl methylcarbamate, commonly known as
carbofuran; 2-isopropoxyphenyl methylcarbamate, commonly known
as propoxur; 1-naphthyl methylcarbamate, commonly known as
carbaryl; 2,3-isopropylidenedioxyphenyl methylcarbamate, commonly
known as bendiocarb; and the like.
In a further embodiment of the invention, the active

2l~s289
component will preferably be two or more ectoparasiticidal active
compounds comprising an organophosphate in combination with one
or more pyrethroids, organochlorines and carbamates. The
organophosphates, pyrethroids, organochlorines and carbamates can
include those compounds previously described.
To the extent that the ectoparasiticidal active
compounds may exist as optical or geometric isomers, all isomers
and racemic mixtures are understood to be included herein. All
possible other isomeric forms of the compounds are also included
herein.
The ectoparasiticidal active compound should be present
in the device which is attached to the animal in an
ectoparasiticidal effective quantity, normally at least approxi-
mately 20% by weight (based on final product) with levels up to
approximately 70% by weight being acceptable. Thus, the polymer
component will be present from 30% to 80% by weight of the final
product. The ectoparasiticidal active compound, if liquid, may
be introduced into the resin by a heating, absorption process,
or if solid, it may first be dissolved in a volatile solvent,
such as acetone, methyl ethyl ketone, methylene chloride and the
like, followed by soaking in the polymer and removal of the
solvent. Generally a blending time of thirty minutes in a high
intensity mixer will produce a homogeneous, free flowing,
polymer/insecticide mixture (called a "dry blend").
It is, of course, to be understood that ultraviolet
light stabilizers such as 2-(2'-hydroxy-5'-methyl phenyl)-
benzotriazole, fillers, lubricants, dyes, antioxidants such as

2l~289
-- 10 --
octadecyl 3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, pigments,
and other inert ingredients may be incorporated into the
formulation from zero to 2% by weight of the final product for
serving their accepted functions which are well known to those
skilled in the art. It has been found preferable to utilize up
to 20% by weight polyvinyl chloride as a processing component to
facilitate production of a free flowing dry blend. All of the
foregoing optional substituents are generally added after the
insecticide has been absorbed into the polymer. High intensity
mixing for approximately five minutes is adequate to provide a
homogeneous mixture incorporating the optional components.
The previously compounded dry blend may be formed into
an acceptable shape, such as an ear tag, for attaching to an
animal by various techniques well known to those skilled in the
art. Extrusion, injection, and compression molding are all well
known techniques, with injection molding being the preferred
method of forming the preferred form of the device, namely, ear
tags.
As a general process of preparing the components into
a dry blend for molding processes, polyurethane beads or pellets
are milled or ground to finer than approximately a 16 mesh size.
The ground polyurethane is placed in a high intensity mixer and
when the powder reaches a temperature of approximately 180 F,
the ectoparasiticidal compound is added until completely absorbed
over a five to seven minute period. The mixture is removed from
the mixer and placed in a cooled ribbon blender. As the mixture
cools, other and optional ingredients such as polyvinyl chloride,

21 SS289
-- 11 --
pigments, fillers, lubricants and antioxidants can be added. The
resulting free-flowing powder can be processed and molded in a
well known manner.
As an alternative to the molding techniques described
above, the insecticidal device can be formed by coating the
polyurethane resin, ectoparasiticidal active compound and
optional additional components onto a substrate. The substrate
is typically but not necessarily inactive and can be selected
from any of various suitable materials such as porous or
homogeneous plastic sheets, fabrics made of natural or synthetic
fibers or combinations thereof, natural or synthetic leather,
plastic mesh pattern cloths, coated fiberglass screening or
cloth, and coated plastic screening. Substrates are typically
used in those applications where added mechanical strength is
needed for the final product because of very high loadings of the
ectoparasiticidal compound in the polyurethane polymer matrix.
It may also be desirable to use the higher mechanical strength
substrates with comparatively lower loadings of ectoparasiticidal
compound in those instances where high strength is necessary at
the point of attachment of the device to the animal.
Among the various suitable processes which can be used
for coating the substrates with the polymer and ectoparasiticidal
compound are spread coating, dip coating and extrusion or
coextrusion lamination techniques. As but one example, the
polyurethane resin, ectoparasiticidal active compound and
optional additional components can be dissolved in volatile polar
solvents such as tetrahydrofuran, dimethyl formamide, dioxane,

2ls~289
- 12 -
acetone, methyl ethyl ketone, chloroform and the like, or
mixtures of such solvents. The solution is then applied to the
appropriately shaped substrate using suitable knife coating,
roller coating or transfer coating processes. The mixture can
be applied to the substrate as a single layer or multiple layers
with the solvents being removed from the product in drying ovens.
In dip coating processes, the substrate is cut to shape
and is dipped into the solubilized mixture which has the desired
flow properties to obtain a smooth coating and to diminish the
tendency for the solution to drip from the substrate prior to
drying. Following drying, the coated substrate can again be
dipped into the mixture to build up the necessary coating
thickness.
The substrates can also be coated by melting the
polyurethane resin, ectoparasiticidal active compound and
optional additional components in an extruder and forcing the
melt through a slit die onto the substrate. The coated substrate
can then be cooled on rollers followed by cutting into the
desired shape of the final product such as an ear tag.
A preferred range for polymer and insecticide is 40%
to 60% by weight polymer and 30% to 60% ectoparasiticidal active
compound with the balance comprising polyvinyl chloride (up to
20% by weight) and up to 2% by weight inert ingredients such as
antioxidants, ultraviolet light stabilizers and pigments, all
well known to those skilled in the art (all weight percents based
on final product).
The following examples are illustrative of some of the

21S5289
- 13 -
possible variations which are contemplated as being within the
scope of the invention.
Example 1
Various polymer compositions incorporating Diazinon
insecticide were prepared according to the absorption procedure
previously described utilizing technical grade (88% purity by
weight) Diazinon and quantities within the preferred range. Ear
tags were formed from the dry blend by injection molding.
Table I summarizes the composition formulations of the
ear tags made according to this example.

2l55289
-- 14 --
U~ ~ o o ~
0 ~ a _ o
~o o oo ~o ~
N 0 0 0 0
~ r~ O
0 l~i ~i o o
U ~ ~ ~
'i
~ X
l~ O ~O
O ~.i ~ _ U~
c U~
~U '
I_ ~ Nl ~ ~
t u~ ~ . . ~
-
'i , . o~
~ ~ -- r
A C
X .. ~ . I _~
0 88 ~ rA C O~
1~ N
O
'~ A t~ n
J~ ~ ., ~ ~; ~ I

- 21SS289
- 15 -
Table II provides a summary of the insecticide released
during field trials utilizing the tags identified in Table I.

Table 11
Field Trials
~verage Release Rate Of Diazinon
For Ta~s Fro Table I
Lot No. 1 2 3 4 5 6
Location #1 #2 #1 #3 #2 #1 #1 #4 #2 #3 #1 #1
Application
Date 1-9-90 5-15-90 1-20-90 3-30-90 5-15-90 3-30-90 3-30-90 5-17-90 6-27-90 7-26-90 11-12-9011-15-90
Removal Date 7-20-90 10-11-90 7-28-90 8-29-9011-26-90 9-14-9010-20-9010-3-90 10-30-90 11-11-90 3-30-91 4-3-91
Days on Cattle 191 149 189 151 196 168 204 140 126 108 137 138
Total Diazinon
Released (9~ 2.757 3.604 4.162 4.359 4.2594.083 3.812 3.920 3.289 2.696 3.191 2.471
Average Release
Rate mg/day14.424.2 22.0 28.9 21.7 24.318.7 28.0 26.1 25.0 23.3 17.9
1~
C~

21 ~S289
- 17 -
Example 2
Various polymer compositions incorporating Diazinon
insecticide were prepared according to the absorption procedure
using technical grade (88% pure by weight) Diazinon and a dry
blend was obtained. Ear tags were formed by injection molding.
Table III summarizes the composition formulations of ear tags
made according to this example and Table IV provides release rate
data on these same tags.

21 S~2$9
-- 18 --
o o _
o U~l , 0 ~ ~o _ _
,;
.,
' 0 , o~ _ ~ U~ ~
~ : 0
: . X
,_ ~ IL '~1 _ : : ~o o
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Table IV
Field Triul~
Average Relense Rate Of Dia~inon
For Tags Fro Table 111
Lot No. 1 2 3 4 5
Location #1 #1 #2 #3 #3 #2 #3 #2 #3 #4 #2 #1
Application
Date 3-31-90 3-30-90 3-23-905-15-90 5-15-90 3-27-906-27-90 7-26-90 6-27-90 5-25-906-23-90 11-10-90
Removol Date 7-21-90 9-15-90 8-29-90 10-31-9010-1-90 8-29-90 10-30-9011-11-9010-30-90 10-29-90 12-01-90 4-01-90
Deys on Cattle 112 169 159 168 140 155 126 108 126 157 161 141
Total Dia~inon
Released (g)2.393 3.177 3.383 3.3084.860 4.no 2.7582.807 3.327 4.067 4.061 2.252
Average Release
Rate mg/day 21.4 18.8 21.3 19.7 34.7 30.5 21.926.0 Z6.4 25.9 25.2 16.0
~'
cr~
oo
C~

2 1 Ss289
- 20 -
Example 3
Ear tags from Lot 4 of Example 1 (Tables I and II) and
from Lot 2 of Example 2 (Tables III and IV) were attached to the
ears of cattle in herds located in New Mexico and Texas. One tag
per animal was used to determine the efficacy against horn flies.
In both trials, an untreated cattle herd was located within the
vicinity of the tagged herd. On the application day, and weekly
thereafter, horn fly counts were taken on at least ten randomly
selected tagged and untagged animals. The results are summarized
in Table V.
From this data it is evident that a surprising long
term efficacy can be achieved with only one tag of the present
composition, even under very high fly populations (infestation)
for a period of at least six months.

21~289
-- 21 --
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- 2I ~289
- 22 -
ExamplQ 4
Ear tags containing 46 wt.% of a polyurethane resin,
46 wt.% of technical grade Diazinon, 6 wt.% of PVC resin and
2 wt.% total of stabilizers, dyes, and pigments were prepared
using the following resins previously identified:
Tag
ReAin
2 B
3 C
4 D
56 E
An efficacy trial with all tags was conducted in Alabama. As in
Example 3, only one tag per animal head was employed, and an
untagged control herd was kept in the vicinity of the tagged
herds. An average number of horn flies from at least ten
randomly selected animals in each herd, taken on the application
date and every two weeks thereafter, are listed in Table VI.

21 ~S289
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21 SS28~
- 24 -
BxamPle 5
Using various techniques, insecticidal ear tags were
prepared comprising various polyurethane resins and various
pyrethroids. Table VII summarizes the composition formulations
and Table VIII provides the preparation methods, number, and
average weights for these tags.

21 SS2~9
-- 25 --
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' 2lss289
-- 26 --
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2lss289
- 27 -
Exampl~ 6
Ear tags from Lots 3, 4, 11 and 7 were compared with
a commercial ear tag available from Fermenta Animal Health
Company under the trademark Ectrin and containing 8% by weight
fenvalerate in a PVC matrix and utilizing 28% by weight di-2-
ethylhexyl adipate as a plasticizer. The tags were attached to
ears of cattle in herds located in Texas. Two tags per animal
were used to determine the efficacy against horn flies using the
testing procedures previously described. The results are
summarized in Table IX and demonstrate that surprising long term
efficacy was obtained with the pyrethroid/polyurethane tags.

21~S289
-- 28 --
Wv N O O O O O O O O O O O O O
c ~ N 00 _ æ o0 0o u~ ~ ~orl N N N
o o o o ~t u~ `o NO ON O O O O ~-1
E ~
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V
vc ~ J ~
o _ ~ _ N ~ U~ `O ~ 0 O` O -- ~ a
# ~ ~

2ls~28y
- 29 -
Example 7
Ear tags comprising endosulfan and polyurethane in
amounts within the ranges previously described are prepared using
compression molding techniques, also as previously described.
The composition formulations for the tags are summarized in Table
X below.

Table X
Polyurethane Tags ~ade ~ith Varying Quantities
of Resin E and Endosulfan Insecticide
Composition. ~t.%
Lot No. 1 2
Resin E 58.4 38.4
Endosulfan~98.1X)40.0 60.0
UV and antioxidant
Stabil kers -- 1.0 1.0
(approx. 1:1
by ~eight~
Colorants, Pigments, 0.6 0.6
Lubricant

21 S~289
The method of preparing a device for protecting animals
from insects according to the present invention comprises
combining an ectoparasiticidal active component with a polymer
which is the reaction product of 4,4'-diphenylmethane
diisocyanate, polytetramethylene glycol and 1,4-butanediol, and
then forming the combination into a device which is attachable
to an animal, such as an ear tag. The resin and
ectoparasiticidal compound are preferably combined by utilizing
30% to 80% by weight polymer and 20% to 70% by weight of the
compound. The most preferred method utilizes approximately 30%
to 60% by weight of the ectoparasiticidal compound, 40% to 60%
by weight polymer, and up to about 20% by weight polyvinyl
chloride with up to 2% by weight inert ingredients, such as anti-
oxidants, W stabilizers, and pigment.
The invention also encompasses a method of protecting
non-human domestic animals from ectoparasites which comprises
attaching to the animal a device formed from a polymer which is
the reaction product of 4,4'-diphenylmethane diisocyanate,
polytetramethylene glycol and 1,4-butanediol, which polymer has
been mixed with up to 70% by weight of an ectoparasiticidal
active compound. The preferred method utilizes the percent by
weight ranges previously specified for the method of preparing
the device according to the invention. All percentages are by
weight based on the final product.
The ectoparasites which are controllable in accordance
with the present invention include flies such as horn, face,

21 SS289
- 32 -
stable and house flies; wingless flies known as keds which
frequently are an ectoparasite for sheep; lice; fleas; ticks;
mites; grubs and the like.
Among the animals which can be protected using the
method of the invention are bovine, ovine and porcine animals,
as well as other livestock such as horses and poultry and fur-
producing animals such as mink and fox. It is to be understood
that the invention is not limited to protection of the animals
specified but can include other animals as well.
From the foregoing it is apparent that the device and
methods of the present invention provide for a highly effective
way of protecting domestic animals from insects such as horn
flies for a prolonged period of time. The devices according to
the present invention are able to support surprisingly high
loadings of insecticides. Equally surprising is the fact that
the devices remain dry without exudation of insecticide, even
after prolonged storage at elevated temperatures. Also,
notwithstanding the unusually high loading of insecticide, the
tags remain flexible and strong for long retention on the animals
being protected.
Because of the high loadings of ectoparasiticidal com-
pound(s) which can be obtained in the devices of the present
invention, smaller devices can be used to provide effective
control of ectoparasites on animals. The use of smaller devices
is particularly advantageous because it allows the devices to be
worn by smaller and younger animals with less likelihood of
undesirable physical changes in the animals. For example,

2ls~289
smaller ear tags can be worn by calves and sheep without causing
drooping of the ear of the animal or causing enlargement of the
attachment opening in the ear with potential resulting loss of
the ear tag. In addition, the smaller sizes obtainable for the
devices allows a single device to be used for smaller animals and
two or more devices used for larger animals or heavily infested
areas. The smaller devices can thus be used for a wider range
of applications, thereby allowing for production of a fewer
number of standard sized devices instead of numerous different
sizes of devices.

Representative Drawing

Sorry, the representative drawing for patent document number 2155289 was not found.

Administrative Status

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Event History

Description Date
Inactive: IPC from MCD 2006-03-11
Time Limit for Reversal Expired 2003-08-04
Letter Sent 2002-08-02
Grant by Issuance 1998-12-01
Inactive: Final fee received 1998-07-09
Pre-grant 1998-07-09
Notice of Allowance is Issued 1998-05-04
Notice of Allowance is Issued 1998-05-04
Letter Sent 1998-05-04
Inactive: Status info is complete as of Log entry date 1998-04-27
Inactive: Application prosecuted on TS as of Log entry date 1998-04-27
Inactive: Approved for allowance (AFA) 1998-03-31
Request for Examination Requirements Determined Compliant 1996-03-14
All Requirements for Examination Determined Compliant 1996-03-14
Application Published (Open to Public Inspection) 1996-02-11

Abandonment History

There is no abandonment history.

Maintenance Fee

The last payment was received on 1998-07-15

Note : If the full payment has not been received on or before the date indicated, a further fee may be required which may be one of the following

  • the reinstatement fee;
  • the late payment fee; or
  • additional fee to reverse deemed expiry.

Patent fees are adjusted on the 1st of January every year. The amounts above are the current amounts if received by December 31 of the current year.
Please refer to the CIPO Patent Fees web page to see all current fee amounts.

Fee History

Fee Type Anniversary Year Due Date Paid Date
MF (application, 2nd anniv.) - standard 02 1997-08-04 1997-07-18
Final fee - standard 1998-07-09
MF (application, 3rd anniv.) - standard 03 1998-08-03 1998-07-15
MF (patent, 4th anniv.) - standard 1999-08-02 1999-07-20
MF (patent, 5th anniv.) - standard 2000-08-02 2000-07-20
MF (patent, 6th anniv.) - standard 2001-08-02 2001-07-19
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
FERMENTA ANIMAL HEALTH COMPANY
Past Owners on Record
RUDOLF J. KRZEWKI
STANLEY ACKERS
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Description 1996-02-10 33 803
Abstract 1996-02-10 1 31
Claims 1996-02-10 5 175
Claims 1998-03-10 5 152
Commissioner's Notice - Application Found Allowable 1998-05-03 1 164
Maintenance Fee Notice 2002-09-02 1 177
Correspondence 1998-07-08 1 33
Prosecution correspondence 1995-08-01 9 316
Prosecution correspondence 1996-03-13 1 42
Examiner Requisition 1997-08-25 3 80
Prosecution correspondence 1996-04-29 1 31
Courtesy - Office Letter 1996-05-07 1 48
Prosecution correspondence 1998-02-25 1 47
Prosecution correspondence 1998-02-25 6 183
Prosecution correspondence 1998-03-05 3 101